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                 K R I S T E N' S    C O L L E C T I O N
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This work is copyrighted to the author © 2008.  Please
don't remove the author information or make any changes
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Jan and Lynn
by Karen Shane (address withheld)

***

Lynn suggests that a young man let her make a Halloween 
costume for him since he had none. (MF, Fdom, teens, 
tg, mc, bi)

***

Lynn finished hooking the last garter to the coffee 
colored nylons and admired the sleek look of the sheen 
on his closely shaven legs. He looked at the reflection 
in the dressing table mirror and couldn't help but 
smile at the feminine figure peering back at him. His 
hair was long, straight and blond and he had skillfully 
brushed and teased it into a sweeping page boy. His 
brows had been perfectly plucked and added to his 
striking appearance. Years of training in makeup 
application showed through in the beautiful face that 
glanced back at him from the mirror.

After donning a pretty powder blue lace bra that 
matched his wispy garter belt, Lynn pressed his 
testicle into his abdomen and pulled his flaccid male 
member back between his legs. He artfully slid a pair 
of matching Lycra hip huggers into place and completed 
the transformation. Crossing the room to the huge 
closet, Lynn selected a darker blue lace trimmed slip 
and a simple knee length heather knit dress to complete 
the ensemble. As he put these garments on, he couldn't 
help but reflect upon the first time he had ever worn 
garments such as these.

He had only been fourteen years old when his parents 
were killed in an automobile accident. After the 
funeral he found himself being taken in by an aunt and 
uncle living in another state. It really wasn't that 
bad though because his uncle spent most of the time on 
the road as a truck driver and his new guardians had a 
daughter a year older than himself. He recalled 
arriving in late autumn with his little suitcase and 
memories. 

Janet was with her mother when they picked him up from 
the bus stop. His aunt quickly introduced the two and 
then explained that his uncle was on the road as usual. 
The three of them returned to his new home and Lynn 
recalled how striking Janet had been on that first 
meeting. 

As he unpacked what little he had with him Janet sat 
quietly in a corner of the room while his aunt 
flittered around the room. He remembered how Janet 
invited him to accompany her to a school Halloween 
costume party and how he hesitantly told her he had no 
costume to wear. It was his aunt who quickly suggested 
that perhaps Janet could fix him up with something 
suitable.

Lynn thought back how Janet had taken him to her room 
and showed him the costume she was going to wear. She 
was going to attend the party as an 1800's southern 
debutante and suggested he could also go in the same 
kind of costume. She had reasoned with him and 
explained that she had everything to make a second 
costume identical to hers.

Lynn was reluctant to accept the offer but he recalled 
how Janet busied herself with selecting various 
articles from her drawers and closet. He thought fondly 
of how she persuaded him to try on the old gown she had 
purchased at a Goodwill store. He had slipped it on 
over his own clothing and remembered the sparkle in 
Janet's eyes as he stood before her.

Aunt Ruby had to return to work and he recalled how the 
two of them had remained in Janet's room the rest of 
the day. He removed the gown and Janet coaxed him into 
trying the complete outfit on so she could determine 
what else she would need to do. Lynn smiled to himself 
as memories of the first time he wore Janet's dainty 
undergarments returned to him.

Janet had given him an old cotton brassiere, a pair of 
white nylon tricot panties and layers of petticoats to 
put on. She had instructed him to return to his own 
room and put on the lacy attire and then return to her 
room. He recalled striping his own clothing from his 
body and standing nude in the room as he pulled the 
panties up his legs. The sensation of nylon against his 
body created a tingling pleasure and he remembered his 
first erection. Quickly, as if to hide the hard on, he 
pulled the billowing petticoats into place and adjusted 
the waist band slightly above his panty line. He put 
his arms into the bra and was just slipping it on when 
Janet had entered his room.

Warmly he recalled how she matter-of-factly crossed the 
room and assisted him with hooking the bra behind his 
back. He followed her back to her bedroom and stood 
quietly as she fumbled in one of her dresser drawers 
and then produced a pair of foam inserts for the bra. 
After inserting the two pads in his cotton bra, Janet 
picked up the gown and held it over Lynn's head. He 
wiggled into the dress and was smoothing it in place as 
she zipped up the back.

Both teenagers giggled with delight and marveled at 
what a pretty girl Lynn portrayed. Janet suggested they 
both go to the Goodwill store and see if they could 
find another gown similar to hers. She even persuaded 
Lynn that it would be a good idea for him to wear the 
undergarments he would be wearing when he tried the 
gown on. She convinced him that to get a good fit it 
would be necessary, and Lynn was already captured by 
her enthusiasm so he agreed to the suggestion.

Janet had helped him out of the gown and was pulling 
the petticoats from his body when she noticed his 
obvious problem. She produced a panty girdle from one 
of her drawers and handed it to him. Lynn quickly 
pulled the garment on and accepted a slip that Janet 
held out for him. She disappeared into her closet as he 
put on the silky garment and then returned with a black 
pleated skirt and a frilly lace blouse.

Janet even had a pair of anklets and penny loafers to 
complete his outfit and Lynn recalled warmly at how the 
clothes and shoes fit him so well. Memories of the trip 
to the Goodwill store floated back as Lynn thought 
about how Janet brushed his hair into a feminine 
fashion and then grabbed a couple of coats from her 
closet.

They both had boarded the bus for the short trip to 
town and Lynn was amazed at how easily he was able to 
pass for a young school girl out on an ordinary 
shopping trip. They were able to find another gown and 
Janet had assured him she could alter it properly 
before the party.

He recalled how they both wandered from store to store 
and how he delighted in the reflection of the two young 
girls beaming back at him from the windows. He also 
thought about how it had gotten so late and when they 
returned home Aunt Ruby was already home from work. 
Somewhat surprised at his appearance, Aunt Ruby 
accepted her daughter's explanation of the shopping 
spree for the costume party and how it was necessary 
for Lynn to try on the gown. He even recalled how Aunt 
Ruby seemed to appear happy at the two of them becoming 
such good friends so quickly.

Lynn sat at the dressing table in his apartment and let 
his thoughts float again to Janet's expert training. He 
remembered how he had made such a hit at the party. In 
fact, no one realized he was not a girl. Janet 
introduced him to everyone and told all of her friends 
that her cousin would be living and going to school 
there from now on. The way he was dressed and the name 
his parents had given him all seemed to add to the 
pleasure he had that night. 

Aunt Ruby loved the way Lynn and Janet got along so 
well. She had always wanted more children, especially 
daughters, but had not been able to have anymore after 
Janet was born. She was the one that brought the 
suggestion up to the two when she hinted that Lynn 
could be enrolled in the school as a girl if he so 
wished. Janet and Lynn thought the idea was fantastic. 
Lynn's name would let him get away with it, and Janet 
welcomed the idea of having a sister to share 
everything with. Lynn remembered how he felt dressed in 
the period costume and the two of them returned home 
that night. Aunt Ruby had waited up for them and they 
all sat around the living room talking of the fun they 
had had.

When she had suggested the idea, Lynn recalled how 
attached he had become to Janet and how he wanted 
nothing more than to please her. He readily accepted 
the idea and the three of them quickly put a plan into 
effect. Since the next day was Saturday, Aunt Ruby 
suggested they all go shopping and pick up things 
necessary for Lynn to make the complete transformation.

Janet promised Lynn that she would provide everything 
he needed for right now and the two disappeared 
upstairs to her room. Still in their costumes, Lynn 
thought about how Janet had given him his first 
nightgown and informed him that if they were really 
going to fool everyone, he would have to start living 
and acting full time as a girl. 

Janet had been the one to suggest they get into their 
pajamas and she would give him his first lesson in make 
up. Lynn thought about how he had reluctantly taken the 
gown off but had left the panties and bra on as he put 
on the waltz length tricot nightgown Janet had 
provided. He even remembered that was the night he 
experienced his first orgasm as he slid the petticoats 
down his panty covered body. It had been electric, but 
he recalled how embarrassed he had been when Janet saw 
the stain. 

Janet taught him how to use a sanitary napkin and how 
to adjust the belt around his waist. She even came up 
with the idea of tucking his member back between his 
legs and Lynn thought about how little that had changed 
from those days. She had given him some new panties and 
this time they were much prettier than the plain white 
nylon tricot ones she had previously provided for the 
costume. Lynn had the napkin in place and pulled the 
pastel pink panties on. 

Janet had him lay on the bed and she plucked his 
eyebrows for the first time. His thoughts came quickly 
back to the present as he heard the telephone ring. 
Lynn picked up the phone and heard Janet's voice on the 
other end. She had called to let him know she was going 
to work a couple of hour's overtime and would be home 
late. After thanking her for calling he replaced the 
phone and went out into the living room.

Tucking his legs under him, he sat down on the couch 
and thought about the trip to town so many years ago. 
Aunt Ruby, Janet and Lynn had all dressed to the hilt. 
Janet had provided the poodle skirt he wore that day, 
the one that still hung in his closet and provided so 
many memories. He remembered how he had awakened early 
and gone to her room. She too was just getting up and 
was at her dresser selecting clothing for the day. He 
thought about how he stood in the doorway and she had 
looked up at him. 

Janet had smiled so innocently and then beckoned for 
him to come in. He had crossed over to the dressing 
table and smiled as he thought back to how she reached 
over and placed her hand on his groin. He was still 
wearing the sanitary belt she had given him the night 
before and he recalled how his penis grew comfortably 
erect in it as she slowly rubbed the nightgown against 
his panties. 

The feeling of Janet's hand massaging the sanitary 
napkin and the confines of the bra he was wearing 
brought about his second orgasm. Lynn smiled inwardly 
at the memories of these feelings. He thought about how 
he shuddered as the warm liquid shot from his penis and 
filled the void between his body and the napkin. He 
remembered how Janet sensed his relief and how she 
stopped her hand movement as he exploded. She was 
smiling at him when he opened his eyes and he 
remembered how her other hand was between her own legs. 
She too had experienced an orgasm and the two just 
remained motionless for a minute.

Janet had quickly recomposed herself and was rummaging 
through her drawers when Aunt Ruby entered the room. 
Lynn thought about how he felt a little guilty when she 
had come in the room, but he remembered how she had 
seemed so excited with the coming events of the day. 
She urged the two to dress quickly and they would be on 
their way. She had said something about getting out of 
the house before his uncle returned and then left the 
room.

Janet provided Lynn with a pile of undergarments and 
instructed him to change into whatever he liked and to 
put the rest in his drawer for later use. Lynn recalled 
how he carried the items back to his room and then 
stripped from the nightgown, panties and bra. Janet had 
provided him with a box of napkins so he replaced the 
soiled one he was wearing. After tucking himself back 
properly, he selected a pair of full length lace 
trimmed panties and a pretty embroidered brassiere. 

With affection he thought about how he slowly pulled 
the panties on and then placed the bra around his 
chest. After hooking the clasps, he slid into a nylon 
slip and then inserted the foam pads in the bra. He 
recalled how he returned to Janet's room and she had 
the poodle skirt and a fluffy yellow angora sweater lay 
out on the bed. 

Lynn pulled the skirt on and then placed the soft 
angora sweater over his head. The effect was dramatic! 
He couldn't believe how sensuous he felt with the 
sweater clinging in all the right places. He even 
remembered how Janet commented on the outfit and told 
him since he looked so good in it, he could keep it as 
his own.

He thought about how the three of them drove into town 
in the old Packard and about how they all had such a 
good time. He recalled Aunt Ruby taking him from 
department stores to shoes stores and even some 
specialty lingerie stores. The thoughts of that day 
provided warm loving memories and he lingered with them 
a while longer.

Lynn traced his memories of that day and thought about 
how they returned home. Janet had been so eager and had 
helped him with all of the packages. She would put a 
few things away and then find something among the items 
that she wanted him to model for her right away. He 
recalled how the two of them enjoyed so much sharing 
that day.

He thought about how he had somehow managed to complete 
school without anyone else ever finding out about his 
secret. And about how he joined Janet at the state 
college and the two of them were able to share a dorm 
room. Thoughts of his first semester brought back other 
memories too.

He remembered how Janet got him the part time job in 
the pizza place. Then he recalled the first blind date 
she fixed him up with at college. The two of them were 
doubling and would be going to a drive in. The memory 
of the poodle skirt again flooded Lynn's mind. He 
recalled how he had finished taking a long hot bath 
after the last class that day. Janet had returned to 
the dorm and was drawing a bath for herself when she 
told Lynn about the date.

He was excited too. Although he had met young men 
during his last year in high school he did not date 
because Janet had gone off to college and he didn't 
feel comfortable without her around. Now he would get a 
chance to find out what it was like, and she would be 
close by to offer support if it was needed.

Lynn thought about how he stood in front of their 
shared dresser with the towel wrapped around him. The 
memories of selecting everything and dressing filtered 
slowly back into his mind. He thought about how he 
first threaded a sanitary napkin into the belt and 
placed that on his body. The routine of tucking himself 
back was so common it seemed natural. Since that was to 
be a special night, he recalled how he had sprinkled a 
fragrant powder on the pad first. 

He remembered the pastel green panties and matching bra 
that he had selected. He also remembered the heavy 
darker green garter belt and seamed stockings that he 
wore that night. Thoughts cascaded back and he recalled 
Janet smiling approvingly at him as she stepped from 
the bathroom. He had been admiring his own appearance 
in the mirror when she finished her bath. Standing in 
just the panties, bra, garter belt and nylons Janet 
dropped the towel from her own body and stepped next to 
him.

Lynn smiled as he remembered how she placed her naked 
body against his and tightly placed her arms around 
him. He recalled how he responded and the erection that 
he got. He remembered how they embraced and fell upon 
the bed. He even thought about how Janet suggested they 
cancel the dates and stay home together, but how she 
relented when he insisted that he have her with him on 
the first time out with a fellow.

He let his mind drift back to that night and remembered 
how Janet picked out an identical outfit in pastel 
yellow. She delighted in his gaze as she placed each 
article on. Lynn helped hook her bra and then they both 
put on matching lace trimmed satin slips. He had worn 
the poodle skirt that night. Janet had given it to him 
a couple of years ago and he still loved it. Patent 
leather dance shoes and a white pullover sweater 
completed the outfit.

Lynn was finishing putting on his makeup when the dorm 
phone rang in the hallway. Janet ran to answer it and 
Lynn selected a pair of ear rings and a necklace to 
compliment the outfit. He had just clasped the ear 
rings when Janet popped in the door and informed him 
their dates were down stairs.

He recalled how they were both a little giddy as they 
descended the steps and took their dates arm. Lynn 
climbed into the back seat of the winged back Ford with 
John as Janet got into the front with her date, Paul. 
Lynn thought about how handsome John had been and about 
how comfortable he tried to make Lynn feel as they 
drove to the picture show. He even remembered when the 
movie finally started how John skillfully put his arm 
around Lynn.

Lynn remembered how John's fingers traced the edge of 
his nylons and lingered for awhile at the garters. He 
thought about how passionately John had kissed him and 
how their tongues darted back and forth. He thought 
about how he felt when Johns hand left the garters and 
started farther up his thighs and then how relieved he 
was when John felt the sanitary napkin and withdrew his 
hand.

He recalled how John had murmured a soft apology and 
then his own boldness when he found his own hand 
against John's manhood. Thoughts of how he nibbled on 
John's ear as he slowly pulled the zipper down drifted 
through Lynn's mind as he realized he was filling his 
panties with an erection. He got up from the couch and 
went into the kitchen.

As he did the few dishes remaining in the sink he 
thought about how he had unzipped Johns slacks and then 
slid his hand into the opening. He recalled the thrill 
he got as he wrapped his fingers around Johns throbbing 
erection. He thought about how Janet had disappeared 
beneath the back of the front seat and he remembered 
how he had boldly began pumping John's erection.

He could recall the soft moaning coming from John as he 
remembered how he stopped and fumbled with the buckle 
to John's pants. The thought of his first experience 
tumbled back and Lynn recalled how he had slid over in 
the Ford and lowered his head to John's eager tool. His 
lips played with the tip of John's dick as he let his 
hand fondle the sweat soaked balls. He thought about 
how John had become so excited and remembered how he 
started lowering his lips over the huge meat. 

Lynn fondly thought of the experience as he finished 
the dishes. He remembered how he had begun sliding his 
lips up and down John's shaft when John exploded in his 
mouth. He also remembered how he squeezed his own 
thighs together and climaxed into the sanitary napkin. 
A smile came to Lynn's face as he returned to the couch 
in the living room.

As he absently thumbed through a magazine, Lynn's 
thoughts drifted back to that date. The boys had 
brought them back to the dorm just after the movie 
ended. They all had to be in before curfew and Lynn 
thought about how Janet and he barely made it to their 
room before the nightly check.

In the dorm room Janet and Lynn carried on like any two 
college girls. Both compared notes and Janet was 
somewhat surprised to hear of the expert fashion Lynn 
handled Johns advances. They had both removed their 
skirts and blouses and were hanging them in the closet 
when Janet turned toward Lynn. As before, they embraced 
each other and Lynn felt a sense of electricity run 
through him as the smooth nylon clad bodies wriggled 
against each other.

Janet's tongue darted into Lynn's mouth as her breast 
pressed firmly against his foam padded bra. Lynn felt 
the erection growing between his legs and he pressed 
his thighs together to contain it. Janet must have 
sensed his urgings and led him to the bed. Both removed 
their slips and let them fall to the floor as they lay 
down on the bed.

Janet placed her breast at Lynn's eager mouth and he 
began suckling her through the brassiere as she let her 
hands drift to his panties. Skillfully she managed to 
thread his firm penis between the leg band of his 
panties and position the rigid cock between both their 
panties. Ever so slowly they began rocking back and 
forth causing the fabric of the panties to caress the 
throbbing member.

As Lynn neared the point of climaxing Janet stretched 
the leg band of her own panties and guided his 
throbbing cock deep within herself. Both feverishly 
pressed against the other and continued to pump as Lynn 
came closer to the edge. They climaxed together and lay 
spent in that position. Lynn recalled how he drifted to 
sleep with Janet on top of him. 

He even remembered how when he woke, Janet was standing 
next to the dresser positioning a hard latex cock to a 
belt contraption. He watched fascinated as she strapped 
it to her groin and turned back towards the bed. Lynn 
thought fondly of how she slowly knelt on the side of 
the bed and urged him with her hands to roll over. 

He dropped the magazine on the coffee table and thought 
about how she had slowly rolled his panties down and 
how he turned his head to watch her rub Vaseline on the 
artificial attachment. Lynn realized he was getting 
excited as he recalled how Janet slowly pressed the tip 
of the dildo to his anus. He thought about how she 
applied a gentle pressure until his quivering opening 
allowed the soft toy to enter him.

Lynn recalled how Janet slowly started moving in and 
out of him until she had managed to insert the full 
length of the dildo in him. He thought about how he had 
become so excited and enjoyed the pleasure the two of 
them had shared. He thought back to that night and 
remembered Janet's increasing tempo and how they both 
climaxed again. 

Well, that was quite a few years ago he thought to 
himself. Both he and Janet managed to graduate from 
college and both found jobs as secretaries in a large 
legal firm. Lynn thought about that first job and how 
it provided a means for them to set up such a nice 
apartment in town together. He also thought about how 
he had gone back to school a few years later and got an 
advanced degree in computer programming.

That was when he met Frank. Lynn thought fondly of 
Frank and how he was the first one besides Aunt Ruby 
and Janet to share Lynn's secret. He and Frank had been 
in a couple of classes together when Frank finally 
worked up the courage to ask Lynn out. Lynn had 
accepted right away and had rushed home from classes 
that day to tell Janet all about it.

He recalled how he shared everything with her and how 
he told Janet that Frank was a pre-med student. Janet 
shared Lynn's happiness and even loaned Lynn a pretty 
new blouse to wear that night. Lynn was so happy and 
pretty when Frank showed up at the door.

They had gone out to dinner and then to a movie. Frank 
had been a perfect gentlemen and was escorting Lynn 
home. They were parked out front of the apartment Lynn 
and Janet shared when he found himself telling 
everything to Frank. Lynn thought back about how calmly 
Frank took the whole thing. After Lynn had told him 
everything, Frank asked when they could go out again 
together.

Lynn thought about how they started dating regular 
after that and then how Frank had started providing the 
female hormones. Lynn remembered when he first started 
taking the hormones and how they had such a dramatic 
effect on his body. He found that within six months he 
no longer needed the foam pads and was able to fill out 
his bras naturally. And, he recalled how his body took 
on a softer, gentler shape.

Frank had been good to him, Lynn thought. It was just a 
shame he had to accept an internship so far away. Lynn 
thought about how they would get together occasionally 
when Frank had a break or was able to take time off 
from the job. He smiled to himself with that thought 
and realized he'd better get the housework done before 
Janet came home.

Since it was his day off, Lynn knew he was expected to 
take care of certain chores. Just like he knew Janet 
was responsible for specific tasks on her days off. 
Lynn got up from the couch and busied himself with 
cleaning the apartment. Occasionally pleasant thoughts 
filtered through his mind and Lynn realized what a very 
lucky person he was. He had almost everything he wanted 
and could live as a beautiful woman. Yes, I certainly 
am lucky he thought.

END

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. 4-million people around the world 
contract HIV every year. You only have one body per 
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 59